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The synthesis of the following compound involves the use of an epoxide. Describe the retrosynthetic analysis of the following antihistamine drug compound through a 1,1, 1,2, or 1,3-diX disconnect. Describe the stages of analysis and synthesis.

The synthesis of the following compound involves the use of an epoxide. Describe the retrosynthetic analysis of the following antihistamine drug compound through a 1,1, 1,2, or 1,3-diX disconnect. Describe the stages of analysis and synthesis.

Introductory Chemistry: An Active Learning Approach
Introductory Chemistry: An Active Learning Approach
6th Edition
ISBN:9781305079250
Author:Mark S. Cracolice, Ed Peters
Publisher:Mark S. Cracolice, Ed Peters
Chapter22: Biochemistry
Section: Chapter Questions
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The synthesis of the following compound involves the use of an epoxide. Describe the retrosynthetic analysis of the following antihistamine drug compound through a 1,1, 1,2, or 1,3-diX disconnect. Describe the stages of analysis and synthesis.

The image depicts the chemical structure of the compound Diphenhydramine, which is commonly used as an antihistamine for relieving allergy symptoms, as a sleep aid, and to alleviate motion sickness. **Structure Explanation:** - **Core Skeleton:** The structure consists of a central oxygen atom (O) connected to a two-carbon chain (ethanolamine backbone), which further connects to a nitrogen atom (N). - **Substituents:** - On the left side, the central carbon is connected to two benzene rings (phenyl groups). - On the right side, the nitrogen atom is bonded to two methyl groups (dimethylamine). **Chemical Representation:** - **Benzene Rings:** Represented by two hexagonal rings, each with alternating double bonds, indicating the aromatic nature. - **Ethanolamine Backbone:** The central part of the structure where the oxygen atom is attached to a carbon, followed by another carbon connecting to the nitrogen. - **Dimethylamine Group:** The nitrogen on the far right is bonded to two methyl groups, denoted by single lines ending in short lines, indicative of carbon atoms bonded to three hydrogen atoms each. This structural representation helps in understanding the arrangement of various functional groups within the Diphenhydramine molecule and is crucial for comprehending its pharmacological properties and synthesis pathways.
Transcribed Image Text:The image depicts the chemical structure of the compound Diphenhydramine, which is commonly used as an antihistamine for relieving allergy symptoms, as a sleep aid, and to alleviate motion sickness. **Structure Explanation:** - **Core Skeleton:** The structure consists of a central oxygen atom (O) connected to a two-carbon chain (ethanolamine backbone), which further connects to a nitrogen atom (N). - **Substituents:** - On the left side, the central carbon is connected to two benzene rings (phenyl groups). - On the right side, the nitrogen atom is bonded to two methyl groups (dimethylamine). **Chemical Representation:** - **Benzene Rings:** Represented by two hexagonal rings, each with alternating double bonds, indicating the aromatic nature. - **Ethanolamine Backbone:** The central part of the structure where the oxygen atom is attached to a carbon, followed by another carbon connecting to the nitrogen. - **Dimethylamine Group:** The nitrogen on the far right is bonded to two methyl groups, denoted by single lines ending in short lines, indicative of carbon atoms bonded to three hydrogen atoms each. This structural representation helps in understanding the arrangement of various functional groups within the Diphenhydramine molecule and is crucial for comprehending its pharmacological properties and synthesis pathways.
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